Gold(I)-Catalyzed cascade cyclization reaction: Highly regio- and diastereoselective intermolecular addition of water and alcohols to epoxy alkynes

被引:86
作者
Dai, Lun-Zhi [1 ]
Qi, Ming-Juan [1 ]
Shi, Yong-Ling [1 ]
Liu, Xu-Guang [1 ]
Shi, Min [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
关键词
D O I
10.1021/ol0713640
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] We have developed a novel access to ketal skeletons through a highly regio- and diastereoselective intermolecular addition of water and alcohols to alkynyl epoxides catalyzed by gold(I). This procedure involves a domino three-membered ring-opening, 6-exo-cycloisomerization, and subsequent intra- or intermolecular nucleophilic addition to a double-bond sequence.
引用
收藏
页码:3191 / 3194
页数:4
相关论文
共 54 条
[11]   Catalytic carbophilic activation:: Catalysis by platinum and gold π acids [J].
Fuerstner, Alois ;
Davies, Paul W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (19) :3410-3449
[12]   Emergence of a novel catalytic radical reaction:: Titanocene-catalyzed reductive opening of epoxides [J].
Gansäuer, A ;
Bluhm, H ;
Pierobon, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (49) :12849-12859
[13]   Room temperature Au(I)-catalyzed exo-selective cycloisomerization of acetylenic acids:: An entry to functionalized γ-lactones [J].
Genin, E ;
Toullec, PY ;
Antoniotti, S ;
Brancour, C ;
Genêt, JP ;
Michelet, V .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (10) :3112-3113
[14]   Relativistic effects in homogeneous gold catalysis [J].
Gorin, David J. ;
Toste, F. Dean .
NATURE, 2007, 446 (7134) :395-403
[15]   Gold(I)-catalyzed intramolecular acetylenic Schmidt reaction [J].
Gorin, DJ ;
Davis, NR ;
Toste, FD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (32) :11260-11261
[16]   Highly selective aerobic oxidation of alcohol catalyzed by a Gold(I) complex with an anionic ligand [J].
Guan, BT ;
Xing, D ;
Cai, GX ;
Wan, XB ;
Yu, N ;
Fang, Z ;
Yang, LP ;
Shi, ZJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18004-18005
[17]   Gold(I)-catalyzed intramolecular hydroamination of alkenyl carbamates [J].
Han, XQ ;
Widenhoefer, RA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (11) :1747-1749
[18]  
Hashmi ASK, 2000, ANGEW CHEM INT EDIT, V39, P2285, DOI 10.1002/1521-3773(20000703)39:13<2285::AID-ANIE2285>3.0.CO
[19]  
2-F
[20]   Gold catalysis: Mild conditions for the transformation of alkynyl epoxides to furans [J].
Hashmi, ASK ;
Sinha, P .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (04) :432-438